[NOTE - Anyone who is just beginning to read my blog, might want to read the following early entries in my blog about my sissy journey before reading this latest entry: A Little More Background - Am I Sure I Should Do This? - I'm Afraid - These - Where It All Started - Then, These - Miss Flo - Caught For The First Time - About My Last Post - Bikini Panties!!! - A Virgin Bride (And Groom) - Exhausted Sissy Needs Stress Relief! - Sissy Marries Cheerleader - Sissy Makes Life With Cheerleader - Cheerleader Discovers Sissy - Cheerleader Accepts Sissy - Cheerleader And Sissy Grow - Cheerleader Asserts Control - Cheerleader Teases Sissy - Cheerleader And Sissy Settle In To New Home. These are the previous posts that tell the story about my sissy journey.]
I venture to guess that this installment about my sissy journey, a long one, may be what many people who have been following my personal story have been waiting for. I have given a lot of thought to how I should go about relating what happened over the course of about four months following the night of my cheerleader's and my 25th wedding anniversary. It seems to me that so much of what I feel I need to convey involves describing thoughts and feelings, rather than actions, and so that is what I intend to attempt to do. And I should emphasize a very important point – living through what I am going to tell was intense, stressful, and extremely difficult. Describing my own thoughts and feelings is a bit easier than those of my cheerleader. Much of what I am attributing to her is based upon her actions, or things she said, more than anything else. I could be altogether wrong about some of what I write about her internal processing of what was taking place in our marriage. And while I am considering the suggestion by someone that I ask her to share a first-hand account of her perspective on this progression we went through together, I am not sure she would want to do so. And for now, at least, I'm afraid to ask her. I’m not sure she would understand being asked to share something so personal in such a public way. So we'll have to muddle along with my narrative.
In the several days immediately following our 25th anniversary, my mind/psyche was, in a word, a mess. Having read what I've written about so far, as well as the hundreds of blog entries I've created, one would be fair to wonder how that could be. Wouldn't one expect that a sissy, such as myself, would be skipping for joy to have a wife who seemed to so eagerly be accepting her sissy husband for the feminine creature he is? Perhaps. But nonetheless, I was a mess. My mind was in constant turmoil over what was happening in our marriage. I felt, more and more, at a loss of control. It was in that context, too, that I believe I began filtering what my cheerleader did and said. She seemed to exert more influence over decisions being made in our life - even small matters such as choosing restaurants. And then, there was the way she treated me. She was so tender and loving, almost as though I was the softer sex in our marriage, rather than herself.
And in bed, each night it seemed as though I was expected to be the woman. And when we made love, there was always a cock, and it was always some man we knew. Don't misunderstand me please. I enjoyed what we did sexually. But we had come so far from me deftly injecting panty play into our lovemaking, to my cheerleader being so open about her fantasy to share a man with her sissy husband.
A few weeks after the night of our 25th anniversary, we hosted a cocktail party at our house for several of my cheerleader's co-workers from the retail store where she worked. Most of her co-workers were women, like herself, who simply wanted some part-time work to occupy their time and make a few extra dollars for spending – mad money. Many of her workmates brought their spouses, but a few were not married and they came alone. There was one guy in particular, named Randall, who stood out to me. First, he was a tall and handsome man. But more than that, I almost immediately sensed that he and my cheerleader had hit it off. He hovered near her for much of the evening. I don't know if what I was observing was real, or colored by what was happening between my cheerleader and me in our marriage. But she seemed to be extremely flirty with Randall. I can still recall thinking at one point in the evening, as I watched them chatting in a small group, that I had never thought of my cheerleader as a flirt before, but that seeing her in this new light, I suddenly realized she had always flirted with other guys at parties. She simply was that way. Now, here in our new life, separated from people who knew her well, and whose opinions mattered to her, my cheerleader seemed (at least to me) to be opening up more.
We had a good time that evening. Her co-workers were very nice and I was happy to see that my cheerleader seemed to be getting along so well with new potential friends. Randall was one of the last to leave and my cheerleader gave him a very warm hug goodbye as they said goodnight. Afterwards, we cleaned up together before going to bed. As I always did at this point, I dressed in pretty lingerie for bed. As I joined my cheerleader, I noticed her large cock dildo lying on her nightstand. Seeing that and realizing what she intended, I returned to my closet to slip on a bra and fill the cups with my breast forms. I then crawled in beside her and snuggled close to her bosom. We cuddled for a few minutes and she thanked me for letting her have her work friends over. What possessed me to say what I was thinking, and had been thinking most of the evening, I am not sure, but I specifically mentioned Randall, and how taken he seemed to be with her. At first, my cheerleader acted like she didn't know what I was talking about, but I pressed her a bit and she finally admitted that he might have a thing for her. I let it drop for the moment, and soon, I was where I usually ended up when we were in bed together with me dressed en femme - between her thighs licking my cheerleader's pussy. And, as things usually went, she eventually invited me to suck a cock for her, to prepare it for fucking her.
As I was sucking the cock she whispered in a needful voice, "I wonder if Randall has a cock that big?" I hesitated a moment at her mention of his name. I had not considered that she would bring him into our fantasy. But then, I continued sucking the cock. And as I did, she asked, "Would you suck him for me?" There was a pause. Then she added, "Randall?" In my state of mind, by this point, I would always say that I would do anything for her. And tonight was no different. So, just like that, Randall, a single man that I could tell wanted my cheerleader, joined us in our bed. And I sucked his cock for my cheerleader. And he fucked her. And she loved it. When it was over and I had gone inside of her, filled her, and then sucked her pussy clean, we fell asleep in each other's arms.
The next day we did not speak of the night before. But there was a tension. Not a bad tension. And not exactly sexual either. But there was something, as if we'd crossed a line? Why did it seem that this new man, someone I had only just met, being brought into our fantasy, created tension for me, whereas I had come to accept my cheerleader fantasizing about our mutual friends during our lovemaking? I couldn’t explain it, but there was something different about the night before.
That next night, as we lay quietly in bed, I spit out what had been on my mind all day. Where we would be today if I had not brought this subject up, I don't know. But, in a way, it doesn't matter. Because I did bring it up. Cuddled up behind my cheerleader, I asked her, "Do you want to?" Those four simple words, asked without specificity, led to so much more than I had considered would develop between me and my cheerleader. She was quiet for a few minutes. “Want to what?” she finally asked. I think she knew what I was asking. Really. But I think she wanted to hear me ask it. "Do you want him to fuck you?" So there it was, after all that had developed over the span of several years of our marriage, I asked my cheerleader if she wanted more than a fantasy. I'd asked her if she wanted another man to fuck her. Her reply was, "Randall?" She knew. I know she did. But she wanted to be sure? That he was who I was referring to? I told her yes, I meant him. I could sense her considering her response now. And that moment of reflection, alone, told me what her answer would probably be. I mean, she didn't dismiss the idea outright, as if I were being ridiculous to suggest such a thing. And yet, I promise you, I did not expect the reply she gave. Instead of saying yes, or no, she asked me, "Would you suck his cock for me?"
Believe me, I was regretting bringing the subject up by this point, but I couldn't undo the conversation now. The tables had been flipped, and in a most uncomfortable way. We engaged in a careful dance of words. I wanted to know if my cheerleader wanted Randall to fuck her. But she was attempting to see where I stood. So I asked her if that was what she wanted. She turned to face me then, and looking into my eyes, she said plainly, "If he is going to fuck me, I want you to suck him for me." I could barely meet her gaze. However, she was so close to my face that I couldn't avoid her. "I will if you want me to," was the answer I gave without thinking it through. In that moment, that is how I felt. She looked into my eyes for what seemed forever before uttering a single word, "Really?" All I could do was nod and whispered back, "Really." My cheerleader then gave me a soft kiss on my lips and said, "Let's think about it." And just like that, the subject was closed, and she turned around and went to sleep. Or, at least she seemed to. I know I didn't. I was so confused by then. Was my cheerleader seriously considering being fucked by another man? And would she really expect me to suck his cock for her? This was made more difficult for me, I think, because we were not discussing her fucking another man as a fantasy idea. We were talking about her fucking a specific man, a man she spent time away from me with, a man who had been in our house only the night before and who my cheerleader had been openly flirting with, who was interested in my cheerleader, and who she was clearly interested in as well.
I don't recall how long I lay awake thinking about what had happened. But, I finally fell asleep. When I woke up, my cheerleader was already out of bed. I remember being thankful for that, as I did not know whether I would be able to look her in the eye. After showering and dressing, I reluctantly went downstairs. I knew that I could not avoid her forever. My cheerleader greeted me cheerfully, almost as if we'd never had the conversation the night before. But she did seem, to me at least, almost too pleasant to me. She kissed me and brushed her hand across my cheek in a loving touch. She began mentioning different errands she wanted to run together, acting as though it was any other weekend day. I remembered thinking that I was relieved that we weren't going to talk about it anymore. And yet, it hung there. All day. In fact, I felt like it was a part of nearly everything we spoke of that day. How do I explain this? I've read many fictional stories about sissies and their wives, where the subject of the wife fucking other men is addressed. There is an edge to the stories - at least the good ones. But they are fantasy. Suddenly, my fantasy was beginning to sound real. My cheerleader seemed inclined to having sex with someone else and wanted me to be a participant. I was not sure how I really felt about that.
Well, we went on like that for a few days. We didn't discuss the subject after that night in bed. Was my cheerleader, as she'd said, "thinking about it?" I couldn't tell. On the following Thursday my cheerleader included a note in my lunch bag. I don't still have it, but I remember it word for word. She wrote, "Dear ____, I think I do. Can I invite him to dinner tomorrow night?" That was it. She wanted to fuck this guy Randall. I didn't know what to do - or what to say. But, I also didn't know how I could deny her this. After all, I was the one who started this thing many years before when I let her know that her husband was, well, a sissy. I knew that she was at work, probably with him, right then. So, without thinking about it much more than that, I sent her a simple text message. "Okay."
How can I describe the emotions I was feeling then? I was unable to concentrate on anything. Trying to work was useless. I decided to go home early and go for a long bike ride. My cheerleader was still at work when I got home, so I didn't have to face that. It was so weird. I was doing what she wanted, but felt embarrassed to face her. Here is what I imagined she was thinking of me - not that I was letting her fuck another man. No. It was more like I was agreeing to suck a man's cock. For her. How was this even going to work? Did she have a plan? I had no idea. Did Randall even know what her intentions were? Had they discussed it? Did she tell him part of the deal, for her, was that I had to suck his cock? Nothing but questions lingered and I was too embarrassed to ask my cheerleader to let me know if she had a plan.
When I returned from my bike ride she was home. She smiled at me as I entered the kitchen. Without a word, she approached me and kissed my sweaty face, something she doesn't like to do. "Go shower," she told me sweetly. She was being sooo nice. And as confused as I was, I realized this much - she was letting me know how much she appreciated what I was agreeing to do for her.
As we ate dinner that night, my cheerleader casually told me that Randall had accepted her invitation to come over the next evening for drinks and dinner around 7. I knew that if I was ever going to address the subject, this was my opening. I asked her if he knew why he was coming over. She smiled and said that she thought so. I then asked if he knew about me, meaning being a sissy, but without saying the word, because we didn't really use it much. Then. She told me that they had talked about it some and that he seemed okay with it. So. There it was. Another person knew my secret. I had shared this secret with only one person. My cheerleader. Now, a man I barely knew had learned of my secret from the person I was closest to in my life – my cheerleader. My stomach sank. I know it may sound stupid. I mean, what did I expect? I'd agreed to my cheerleader's request to invite this guy to dinner. And I understood the reason for the invite. Still, thinking, and knowing, are two entirely different things. Now, it seemed as though this fantasy world we’d built was going to become very real. And I was scared to death. I had no idea how my cheerleader intended to handle the situation. I was completely powerless. Looking back on it though, I can tell you, that powerlessness is a large part of what such an event is about - the complete loss of power, as I was submitting to someone else's desire.
I went to work the next day, although it was a futile effort on my part. I was disconnected from everything, and everyone. I have no idea whether anyone sensed the disorientation that I felt. My cheerleader was off from work, so I knew she would be preparing for the evening. When I arrived home I found that she had done flower arrangements and decorated things beautifully. There were hors d'oeuvres prepared and the dining room table was set with her good china. There was one setting at the head of the table and the other two were across from each other right next to the head seat. I found my cheerleader in our bedroom getting dressed. She was wearing a pretty black bra, panty and garter set, with black stockings attached. I was stunned. I had not considered that she would dress especially to please Randall, but she seemed to be. The dress lying on our bed was a very simple dress - a short black one with spaghetti straps - but it was a sexy one. She asked me to help her step into it and zip it up, and after I did, she asked if I liked it. Of course I liked it, but I was more stunned to think that she was wearing it for Randall, rather than for me.
She told me to hurry up and shower so I could get dressed too. It was obvious that she was very excited about the evening. I couldn't recall when I last saw her quite this way. I remember wondering whether she was excited about being fucked by another man for the first time in over 25 years, or whether it was because her husband was consenting to the event. When I got out of the shower I saw that my cheerleader had shopped for each of us. Lying on the bed next to a pair of grey trousers and dark blue shirt was a white bra and panty set, also with a garter belt and stockings, as well as a white lace slip. So there it was. My cheerleader wanted me in full sissy mode for the evening, at least under my clothes. I dressed and went downstairs to wait for my cheerleader's date. It was about 6:30. She approached me and placed her arms over my shoulders, brushing her fingers along my bra straps and whispered, "Thank you sweetie. You are the best!"
I finally asked her how she planned for it to go. She shrugged her shoulders and said she just planned to let events take care of themselves. I didn't know what to say, so I just said okay. I opened two bottles of wine, one red and one white. I poured my cheerleader a glass of white and myself a glass of red. She kept busy organizing and it struck me then that she was nervous too, but her nervousness seemed more from a heightened sense of expectation and excitement. I was simply a wreck inside, completely flummoxed as to how I should behave. I quickly drank my glass of wine and poured another. Shortly after 7 the doorbell rang. Randall had arrived. This was really happening. I looked at my cheerleader to see if she wanted to answer the door. She asked me to. So, I was going to greet the man who was here to fuck my cheerleader. Almost on automatic pilot at this point I walked to the door and, mustering up the best fake nice face I could manage, I opened the door and greeted Randall. I don't even know how to describe the moment. It was as if we each felt more awkward than the other, and yet he was the one who should have felt the advantage over me, given the purpose of the evening. The irony of his graciousness in thanking me for inviting him over was not lost on me. I still recall how foolish I felt as I uttered my response, "It's our pleasure. Thank you for coming."
I led him to our kitchen where my cheerleader was busying herself, offering him a drink as we walked. He asked for whiskey on the rocks. Natch! Right? When he entered the kitchen and saw my cheerleader in her sexy little black dress he actually let out a low whistle as her called her name. She responded enthusiastically, "Randall! You're here!" She came to him and immediately gave him a warm hug in greeting. Then, as she pulled away, as if she had determined to set the tone for the evening right off the bat, she gave him a soft, somewhat lingering, kiss right on his lips. I stood by dumbly, watching this unfold in front of me. Excusing myself, I told Randall I was going to retrieve a bottle of whiskey. I returned with a bottle of Maker's Mark and a whiskey glass. By my return, my cheerleader had broken away and was setting out her hors d'oeuvres.
I poured Randall a glass of whiskey over ice and handed it to him. He raised his glass to mine and we silently toasted, as if this was the moment of agreement between us that I was handing over my cheerleader to him for the evening. What followed was a fairly awkward silence, one that was finally broken by Randall talking to my cheerleader about some events that had occurred that day at the store where they worked. So, as if I couldn't feel more awkward, I was now not even a part of the conversation. As if sensing what was happening, Randall began asking me questions about my work. And soon, in the oddest twist possible, we were chatting like friends about the things any new acquaintances talk about. And, I had to admit, Randall seemed like a really nice guy.
As we talked my cheerleader put the finishing touches on dinner. Soon, she asked us to help her deliver the food to the dining room. As she reached for the chair at the head of the table, obviously intending for Randall and me to sit on either side of her, facing each other, he beat me to it and held her chair. I watched like a bystander as my cheerleader smiled warmly at this man encroaching upon my responsibility. The dinner my cheerleader cooked was amazing. She is a good cook anyway, but I could tell that she’d made a special effort for Randall and he voiced his appreciation enthusiastically. She was beaming with joy that he liked it so much. I don’t know how to describe the situation. We were three people enjoying a wonderful meal, drinking wine, and engaging in fairly comfortable small talk. And yet, there was this energy at the table, mostly, it seemed to me, coming from my cheerleader and aimed toward Randall. As if she understood that all that was happening – cocktails, dinner, and then after dinner – was necessary to occur, but that there was a real purpose for the evening, and she was looking forward to it.
As we finished dessert, my cheerleader suggested that we retire to our den for another cocktail. Randall began to help clear the dishes from the table, but my cheerleader stopped him, saying he was the guest, and that I’d take care of it. Without argument, I agreed with her that I would clear the dishes. So she and Randall went to the den alone while I cleaned up. I sensed that she orchestrated this so she could be alone with him for a few minutes, so I took my time cleaning the dishes and the kitchen. I was just finishing up when my cheerleader approached me alone. She came to me and hugged me, thanking me for letting her do this. I remember that I didn’t really know what to say to her. I was, frankly, very confused about how this was going to work. I was about to find out. She told me then that she and Randall were going up to our room. She also told me that he wanted it to be just them at first, if it was okay with me. Since I didn’t know what to expect, but realized that my cheerleader was committed to going through with having sex with Randall, I told her I guessed that would be okay. I asked what she wanted me to do. She said just wait, and that she’d let me know when I could join them. And so she and Randall went together to our bedroom to fuck, leaving me alone to wait, and wonder, and imagine what they were doing.
I had fantasized about this happening - many, many times. And my cheerleader and I had played our little games together and they turned me on. But now that a man was going to our bedroom with my cheerleader, I was in turmoil. And yet, I was also oddly relieved. I had been wondering what in the world I was going to do when my cheerleader waited for me, and watched me, suck his cock for her. Sucking the dildos was one thing, but doing a real man was suddenly scaring me. And so, as much as I was torn that I was left out, I was kind of relieved. I sat in our den for a while, quietly wondering if they were doing it yet. And what and how they were doing it. Eventually, in what was one of the most excruciatingly slow passages of time I ever recalled experiencing, I heard a man’s footsteps coming down our stairs. They’d gone up around 10 p.m. It was 2:30 in the morning. So, at least he wasn’t spending the night. I waited for him to leave, but he came to the den to find me. I looked up at him not knowing what to say. He saved me the trouble. He told me he was leaving but said, “Thank you for a wonderful evening.” I, looking back on it, said stupidly, “You’re welcome.” Then he said goodbye and told me my cheerleader wanted me to come up to bed.
After Randall left I had to face the next thing. Seeing my cheerleader after her night of sex with a man. Wondering what to expect, I walked upstairs and entered our bedroom. The room was dark except for some light filtering in from our bathroom. My cheerleader was in bed, sitting up part way against her pillow. I noticed her lingerie was in a pile on the floor. I assumed she was nude. I think she must have been as unsure as I was about what to do next. She smiled at me and said, “Hi.” I said hi back and just stood there waiting for her to tell me what I should do. I really was lost here. She told me to come to bed and so I went to my closet to take off my clothes. As I did, my cheerleader told me to leave on the lingerie I’d been wearing all night.
When I crawled into our bed, she snuggled up to me and hugged me. I just sort of lay there, allowing her to do whatever. She looked at me and asked if I was okay. I told her I supposed so, and asked how she was. What I was really asking was, ‘How was it?’ “Baby,” she whispered excitedly. “It was amazing! I can’t tell you. Thank you so, so much for letting me do that.” She was genuinely appreciative to me. I still didn’t know how to talk about what had happened. I just said, “You’re welcome. I’m glad you enjoyed it.” “I did!” she emphasized for me. “I really did! And so did he I think. God! He was insatiable!” It was like she wanted to talk about it, but was a little hesitant to me. I didn’t know what to say to her. He was insatiable? I said, “Really?” She told me then they’d done it three times! They had been fucking the entire time they were in our room! I was shellshocked. “Really! And guess what?” she asked me. So I bit. “What?” “He is sooo big honey. I’m even a little sore now,” she added. I did not know what to say. I said, probably unconvincingly, “That’s great.” My cheerleader was holding me and rubbing me, her hand on my penis outside of the panties I was wearing, and I was stiff. After a few minutes she told me, “I’d let you, but I am a little sore.” I told her that was okay, although I did want to. Then, she said, “But I’d love it if you’d use your mouth. Gently, like you do. Hmm?” What could I say? Of course I would.
As I moved down to position myself to pleasure her, I remember thinking that what I was about to do was not the same as cleaning my own sperm out of her. This was another man’s cum. And yet, I wanted to do this for my cheerleader. I wanted her to know that I was okay with what she’d done, and this was the best way I could think of to show her. My cheerleader pulled the covers off of her and opened her legs to give me better access. I could sense her watching me, anxious to see me do this for her. It was important to her as well. As I moved toward her recently fucked pussy, I could see that her bush was coated with cum, and there was sperm dripping from her pussy. After all, he’d fucked her three times in just a few hours. I leaned in and licked, coating my tongue with my first taste of another man’s seed. It didn’t taste like mine, but the unmistakable flavor of my wife’s juices comingled with him was there, and I liked that. I licked deeper and then the flow began. Randall’s sperm was running out of my cheerleader now that I’d opened her up with my tongue. She pressed downward on my mouth, silently urging me to clean her out. I really needed no encouragement now. I love pleasing my cheerleader orally - and this time was no exception - for me anyhow. But I think it meant something to her. As I continued to suck cum out of her, slowly fucking her with my tongue, my cheerleader began responding, and I decided that I was going to do my best to bring her to orgasm. She moaned the way she does when I am really getting her going. As she was getting more and more cranked up, she said, “Oh yes baby! God that feels good! I love you so much! I wish you could have sucked his cock for me tonight. I really do! Don’t you?” Honestly! I was trying to get her off and she was asking whether I wanted to suck her lover’s cock. I pulled away long enough to say, “yes,” and then went right back at her. I had to please her this night. I had to! And eventually, I did. She had an earth shattering orgasm, wrapping her legs around my head and squeezing me until I could barely breathe, which can hurt, but I know when my cheerleader does that to me, I have really gotten to her.
When I crawled back up beside her, the film of her juice and another man’s cum coating my face, she kissed me and thanked me again. “Next week, you’ll suck his cock. Okay?” as if she felt it was owed to me, and also letting me know next week was already going to happen. “Okay,” I answered. We fell asleep in each other’s arms and slept late into the morning. When we woke up my cheerleader began going about her day, but there was a new skip in her walk. She was clearly in a wonderful mood because of the night before. As for me, I was still a bit shellshocked. The entire affair had caught me off guard. I had so much to process. And I had to do it with an understanding that this was not going to be a one-time thing. My cheerleader wanted more and wasn’t even discussing that with me. She had decided.
I will tell about the next week, and how things evolved over the next two months of that time frame in our marriage, in my next installment. But, suffice it to say, the emotions and conflict rolling around in my head were only the beginning. My cheerleader had cucked me. I was a cuckold. And no reading cuckold stories, or any fantasy that you can imagine, comes within a whisper of what it feels like when you are actually cucked by your wife with a man who has a cock that actually satisfies her in a way that you couldn’t dream of doing. And it isn’t even really an exhilarating experience when it first happens to you. But it is an experience that you will never forget, and is a shared experience between a sissy and her wife that they will always, in the way that only a sissy and a wife can, cherish.